Browsing by Author "Lin, Hong-Lin"

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Cofacial Versus Coplanar Arrangement in Centrosymmetric Packing Dimers of Dipolar Small Molecules: Structural Effects on the Crystallization Behaviors and Optoelectronic Characteristics
(2016-07-20)
Chou, Shu-Hua
;
Kang, Hao-Wei
;
Chang, Shu-Ting
;
Wu, Kuan-Yi
;
Bazan, Guillermo C.
Two D-pi-A-A molecules (MIDTP and TIDTP) composed of an electron-rich ditolylamino group (D) and an electron-deficient 5-dicyanovinylenylpyrimidine (A-A) fragment bridged together with indeno[1,2-b]thiophene (IDT) were synthesized. These molecules provide an opportunity to examine in-depth the impact of side-chain variations (methyl vs p-tolyl) on the crystallization behaviors, solid-state morphology, physical properties, and optoelectronic characteristics relevant for practical applications. X-ray analyses on single-crystal structures indicate that methyl-substituted MIDTP forms coplanar antiparallel dimers via C-H center dot center dot center dot S interactions and organizes into an ordered slip-staircase arrays. In contrast, p-tolyl-bearing TIDTP shows cofacial centrosymmetric dimers via pi-pi interactions and packs into a less-ordered layered structures. The X-ray diffraction analyses upon thermal treatment are consistent with a superior crystallinity of MIDTP, as compared to that of TIDTP. This difference indicates a greater propensity to organization by introduction of the smaller methyl group versus the bulkier p-tolyl group. The increased propensity for order by MIDTP facilitates the crystallization of MIDTP in both solution-processed and vacuum-deposited thin films. MIDTP forms solution-processed single-crystal arrays that deliver OFET hole mobility of 6.56 x 10(-4) cm(2) V-1 s(-1), whereas TIDTP only forms amorhpous films that gave lower hole mobility of 1.34 x 10(-5) cm(2) V-1 s(-1). MIDTP and TIDTP were utilized to serve as donors together with C-70 as acceptor in the fabrication of small-molecule organic solar cells (SMOSCs) with planar heterojunction (PHJ) or planar-mixed heterojunction (PMHJ) device architectures. OPV devices based on higher crystalline MIDTP delivered power conversion efficiencies (PCEs) of 2.5% and 4.3% for PHJ and PMHJ device, respectively, which are higher than those of TIDTP-based cells. The improved PCEs of MIDTP-based devices are attributed to better hole-transport character.